Acridine-benzene-1,3,5-tricarb-oxy-lic acid (3/1).

In the title adduct, 3C(13)H(9)N·C(9)H(6)O(6) or (acr)(3)(btc), associ-ations of one btc and three acr molecules linked by O-H⋯N hydrogen bonds occur. C-H⋯O interactions also occur, resulting in a cyclic hydrogen-bonded synthon R(2) (1)(6). The acr mol-ecules and the btc mol-ecules also form slipped or offset π-π stacking inter-actions [centroid-centroid distances of 3.5212 (17) Å for btc rings and 3.703 (2) and 3.731 (2) Å for acr rings]. Together these inter-actions lead to a three-dimensional network.

Related literature

For background to proton-transfer compounds including acridine, see: Tabatabaee et al. (2009 ▶); Eshtiagh-Hosseini et al. (2010 ▶). For background to co-crystals, see: Dale et al. (2004 ▶).

Experimental

Crystal data

3C13H9N·C9H6O6

M = 747.77

Triclinic,

a = 12.031 (2) Å

b = 13.113 (3) Å

c = 13.220 (3) Å

α = 77.44 (3)°

β = 71.43 (3)°

γ = 72.23 (3)°

V = 1865.9 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.45 × 0.3 × 0.2 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: numerical (X-RED and X-SHAPE; Stoe & Cie, 2005 ▶) T min = 0.964, T max = 0.980

15233 measured reflections

7305 independent reflections

3826 reflections with I > 2σ(I)

R int = 0.088

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.218

S = 0.95

7305 reflections

526 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.34 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810050233/om2368sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050233/om2368Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

3C13H9N·C9H6O6	Z = 2
Mr = 747.77	F(000) = 780
Triclinic, P1	Dx = 1.331 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.031 (2) Å	Cell parameters from 7305 reflections
b = 13.113 (3) Å	θ = 2.1–26.0°
c = 13.220 (3) Å	µ = 0.09 mm−1
α = 77.44 (3)°	T = 298 K
β = 71.43 (3)°	Block, orange
γ = 72.23 (3)°	0.45 × 0.3 × 0.2 mm
V = 1865.9 (8) Å3

Stoe IPDS II diffractometer	7305 independent reflections
Radiation source: fine-focus sealed tube	3826 reflections with I > 2σ(I)
graphite	Rint = 0.088
Detector resolution: 0.15 mm pixels mm-1	θmax = 26.0°, θmin = 2.1°
φ scans	h = −14→14
Absorption correction: numerical (X-RED and X-SHAPE; Stoe & Cie, 2005)	k = −16→16
Tmin = 0.964, Tmax = 0.980	l = −16→15
15233 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.218	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ2(Fo2) + (0.1227P)2] where P = (Fo2 + 2Fc2)/3
7305 reflections	(Δ/σ)max = 0.001
526 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.1489 (2)	0.0445 (2)	−0.0245 (2)	0.0366 (6)
C2	0.0715 (3)	0.1475 (3)	−0.0249 (2)	0.0401 (7)
H2	0.0842	0.1982	−0.0859	0.048*
C3	−0.0247 (2)	0.1761 (2)	0.0643 (2)	0.0373 (7)
C4	−0.0432 (3)	0.1001 (3)	0.1548 (2)	0.0401 (7)
H4	−0.1069	0.1189	0.2151	0.048*
C5	0.0317 (2)	−0.0032 (2)	0.1564 (2)	0.0373 (7)
C6	0.1281 (2)	−0.0312 (2)	0.0661 (2)	0.0356 (6)
H6	0.1786	−0.1009	0.0668	0.043*
C7	0.2493 (3)	0.0184 (3)	−0.1247 (2)	0.0420 (7)
C8	−0.1130 (3)	0.2841 (3)	0.0637 (3)	0.0475 (8)
C9	0.0045 (3)	−0.0833 (3)	0.2553 (2)	0.0441 (7)
C10	0.5826 (3)	−0.0662 (3)	−0.3125 (2)	0.0487 (8)
C11	0.5902 (3)	−0.0260 (4)	−0.2253 (3)	0.0663 (11)
H11	0.5339	−0.0329	−0.1587	0.080*
C12	0.6791 (4)	0.0227 (4)	−0.2379 (4)	0.0787 (12)
H12	0.6841	0.0483	−0.1795	0.094*
C13	0.7643 (4)	0.0348 (4)	−0.3387 (4)	0.0803 (13)
H13	0.8239	0.0694	−0.3461	0.096*
C14	0.7611 (3)	−0.0025 (3)	−0.4240 (3)	0.0653 (10)
H14	0.8181	0.0066	−0.4897	0.078*
C15	0.6707 (3)	−0.0561 (3)	−0.4144 (3)	0.0483 (8)
C16	0.6635 (3)	−0.0974 (3)	−0.4987 (3)	0.0517 (9)
H16	0.7199	−0.0916	−0.5653	0.062*
C17	0.5721 (3)	−0.1480 (3)	−0.4846 (2)	0.0479 (8)
C18	0.5598 (4)	−0.1925 (3)	−0.5674 (3)	0.0668 (11)
H18	0.6151	−0.1898	−0.6350	0.080*
C19	0.4684 (4)	−0.2389 (4)	−0.5491 (4)	0.0779 (12)
H19	0.4611	−0.2674	−0.6046	0.094*
C20	0.3842 (4)	−0.2449 (4)	−0.4480 (4)	0.0741 (12)
H20	0.3231	−0.2791	−0.4369	0.089*
C21	0.3901 (3)	−0.2020 (3)	−0.3663 (3)	0.0641 (10)
H21	0.3317	−0.2043	−0.3004	0.077*
C22	0.4859 (3)	−0.1532 (3)	−0.3814 (2)	0.0466 (8)
C23	−0.3427 (3)	0.4865 (3)	−0.1242 (3)	0.0475 (8)
C24	−0.2966 (3)	0.3906 (3)	−0.1741 (3)	0.0592 (9)
H24	−0.2266	0.3405	−0.1626	0.071*
C25	−0.3548 (4)	0.3724 (4)	−0.2383 (3)	0.0709 (11)
H25	−0.3227	0.3106	−0.2724	0.085*
C26	−0.4632 (4)	0.4455 (4)	−0.2545 (3)	0.0705 (11)
H26	−0.5022	0.4309	−0.2981	0.085*
C27	−0.5107 (3)	0.5364 (3)	−0.2070 (3)	0.0610 (10)
H27	−0.5827	0.5837	−0.2176	0.073*
C28	−0.4514 (3)	0.5604 (3)	−0.1410 (3)	0.0494 (8)
C29	−0.4945 (3)	0.6528 (3)	−0.0911 (3)	0.0523 (8)
H29	−0.5658	0.7025	−0.1000	0.063*
C30	−0.4323 (3)	0.6719 (3)	−0.0280 (3)	0.0509 (8)
C31	−0.4709 (4)	0.7652 (3)	0.0253 (3)	0.0649 (10)
H31	−0.5416	0.8172	0.0183	0.078*
C32	−0.4067 (4)	0.7791 (4)	0.0856 (4)	0.0781 (13)
H32	−0.4333	0.8404	0.1201	0.094*
C33	−0.2995 (4)	0.7015 (4)	0.0969 (4)	0.0741 (12)
H33	−0.2558	0.7130	0.1383	0.089*
C34	−0.2582 (3)	0.6102 (3)	0.0489 (3)	0.0643 (10)
H34	−0.1877	0.5593	0.0583	0.077*
C35	−0.3234 (3)	0.5934 (3)	−0.0155 (3)	0.0491 (8)
C36	−0.0443 (3)	−0.2948 (3)	0.5167 (3)	0.0533 (9)
C37	0.0199 (4)	−0.2314 (4)	0.5384 (3)	0.0764 (12)
H37	0.0789	−0.2055	0.4830	0.092*
C38	−0.0040 (5)	−0.2087 (4)	0.6387 (4)	0.0904 (15)
H38	0.0384	−0.1664	0.6514	0.108*
C39	−0.0916 (6)	−0.2472 (4)	0.7246 (4)	0.0945 (16)
H39	−0.1058	−0.2311	0.7935	0.113*
C40	−0.1547 (5)	−0.3071 (4)	0.7077 (3)	0.0828 (14)
H40	−0.2131	−0.3316	0.7650	0.099*
C41	−0.1338 (4)	−0.3341 (3)	0.6033 (3)	0.0595 (10)
C42	−0.1932 (4)	−0.3969 (3)	0.5801 (3)	0.0737 (12)
H42	−0.2517	−0.4239	0.6351	0.088*
C43	−0.1683 (4)	−0.4208 (3)	0.4771 (3)	0.0607 (10)
C44	−0.2255 (5)	−0.4863 (4)	0.4478 (4)	0.0911 (15)
H44	−0.2853	−0.5145	0.4999	0.109*
C45	−0.1941 (6)	−0.5077 (4)	0.3462 (4)	0.0977 (17)
H45	−0.2323	−0.5506	0.3285	0.117*
C46	−0.1043 (5)	−0.4659 (4)	0.2667 (4)	0.0879 (14)
H46	−0.0807	−0.4843	0.1974	0.106*
C47	−0.0512 (4)	−0.3994 (4)	0.2888 (3)	0.0697 (11)
H47	0.0040	−0.3684	0.2338	0.084*
C48	−0.0789 (3)	−0.3769 (3)	0.3947 (3)	0.0507 (8)
N1	0.4920 (2)	−0.1125 (2)	−0.2986 (2)	0.0495 (7)
N2	−0.2812 (2)	0.5027 (2)	−0.0623 (2)	0.0495 (7)
N3	−0.0211 (3)	−0.3142 (2)	0.4155 (2)	0.0538 (7)
O1	0.3136 (2)	−0.08203 (19)	−0.12033 (18)	0.0543 (6)
H1	0.378 (3)	−0.092 (3)	−0.193 (3)	0.063 (10)*
O2	0.2668 (3)	0.0870 (2)	−0.20116 (19)	0.0759 (9)
O3	−0.0948 (2)	0.3460 (2)	−0.02961 (19)	0.0640 (7)
H3	−0.173 (5)	0.414 (5)	−0.032 (4)	0.128 (19)*
O4	−0.1941 (3)	0.3119 (2)	0.1420 (2)	0.0805 (9)
O5	0.0707 (2)	−0.1822 (2)	0.24783 (18)	0.0573 (6)
H5	0.041 (5)	−0.239 (4)	0.319 (4)	0.116 (17)*
O6	−0.0735 (2)	−0.0553 (2)	0.33509 (19)	0.0731 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0283 (14)	0.0458 (17)	0.0357 (14)	−0.0116 (13)	−0.0035 (11)	−0.0106 (12)
C2	0.0337 (15)	0.0490 (19)	0.0381 (15)	−0.0152 (14)	−0.0055 (12)	−0.0061 (13)
C3	0.0296 (14)	0.0428 (17)	0.0389 (15)	−0.0075 (13)	−0.0070 (11)	−0.0101 (13)
C4	0.0311 (14)	0.0497 (19)	0.0384 (15)	−0.0122 (14)	−0.0004 (12)	−0.0144 (13)
C5	0.0313 (14)	0.0481 (18)	0.0349 (14)	−0.0162 (13)	−0.0047 (11)	−0.0080 (12)
C6	0.0289 (13)	0.0354 (16)	0.0398 (15)	−0.0067 (12)	−0.0046 (11)	−0.0088 (12)
C7	0.0345 (15)	0.0481 (19)	0.0378 (15)	−0.0114 (14)	−0.0020 (12)	−0.0050 (14)
C8	0.0370 (16)	0.0484 (19)	0.0491 (18)	−0.0041 (14)	−0.0037 (14)	−0.0119 (15)
C9	0.0385 (16)	0.053 (2)	0.0386 (16)	−0.0161 (15)	−0.0015 (13)	−0.0081 (14)
C10	0.0364 (16)	0.057 (2)	0.0453 (17)	−0.0110 (15)	0.0000 (13)	−0.0088 (15)
C11	0.053 (2)	0.089 (3)	0.054 (2)	−0.018 (2)	−0.0018 (16)	−0.023 (2)
C12	0.067 (3)	0.106 (4)	0.074 (3)	−0.025 (3)	−0.018 (2)	−0.031 (2)
C13	0.061 (3)	0.103 (4)	0.089 (3)	−0.035 (3)	−0.021 (2)	−0.015 (3)
C14	0.0436 (19)	0.081 (3)	0.066 (2)	−0.0226 (19)	−0.0032 (17)	−0.007 (2)
C15	0.0354 (16)	0.053 (2)	0.0468 (18)	−0.0074 (15)	−0.0010 (13)	−0.0073 (15)
C16	0.0401 (17)	0.055 (2)	0.0438 (17)	−0.0079 (16)	0.0042 (14)	−0.0023 (15)
C17	0.0476 (18)	0.0427 (18)	0.0438 (17)	−0.0060 (15)	−0.0047 (14)	−0.0053 (14)
C18	0.076 (3)	0.067 (3)	0.053 (2)	−0.017 (2)	−0.0090 (19)	−0.0157 (18)
C19	0.097 (3)	0.074 (3)	0.073 (3)	−0.029 (3)	−0.023 (2)	−0.021 (2)
C20	0.079 (3)	0.067 (3)	0.088 (3)	−0.035 (2)	−0.024 (2)	−0.006 (2)
C21	0.056 (2)	0.065 (2)	0.065 (2)	−0.0260 (19)	−0.0015 (18)	−0.0029 (19)
C22	0.0426 (17)	0.0456 (18)	0.0438 (17)	−0.0107 (15)	−0.0036 (13)	−0.0032 (14)
C23	0.0431 (17)	0.0467 (19)	0.0439 (17)	−0.0102 (15)	−0.0034 (14)	−0.0027 (14)
C24	0.052 (2)	0.054 (2)	0.061 (2)	−0.0074 (17)	−0.0059 (17)	−0.0097 (17)
C25	0.073 (3)	0.073 (3)	0.066 (2)	−0.025 (2)	−0.002 (2)	−0.024 (2)
C26	0.067 (3)	0.084 (3)	0.066 (2)	−0.025 (2)	−0.011 (2)	−0.022 (2)
C27	0.053 (2)	0.068 (3)	0.059 (2)	−0.0140 (19)	−0.0180 (17)	−0.0020 (19)
C28	0.0446 (17)	0.051 (2)	0.0447 (17)	−0.0136 (16)	−0.0037 (14)	0.0000 (15)
C29	0.0459 (18)	0.049 (2)	0.0515 (18)	−0.0075 (16)	−0.0098 (15)	0.0019 (15)
C30	0.0497 (19)	0.0432 (19)	0.0512 (18)	−0.0106 (16)	−0.0060 (15)	−0.0018 (15)
C31	0.063 (2)	0.047 (2)	0.080 (3)	−0.0069 (18)	−0.018 (2)	−0.0091 (19)
C32	0.081 (3)	0.057 (3)	0.100 (3)	−0.018 (2)	−0.018 (3)	−0.027 (2)
C33	0.074 (3)	0.069 (3)	0.091 (3)	−0.025 (2)	−0.024 (2)	−0.022 (2)
C34	0.054 (2)	0.063 (3)	0.077 (2)	−0.0126 (19)	−0.0213 (19)	−0.009 (2)
C35	0.0477 (18)	0.049 (2)	0.0477 (18)	−0.0162 (16)	−0.0076 (14)	−0.0026 (15)
C36	0.064 (2)	0.052 (2)	0.0419 (17)	−0.0191 (18)	−0.0093 (15)	−0.0019 (15)
C37	0.095 (3)	0.081 (3)	0.066 (3)	−0.045 (3)	−0.019 (2)	−0.005 (2)
C38	0.124 (4)	0.090 (4)	0.077 (3)	−0.043 (3)	−0.035 (3)	−0.019 (3)
C39	0.141 (5)	0.093 (4)	0.055 (2)	−0.032 (4)	−0.025 (3)	−0.019 (2)
C40	0.111 (4)	0.079 (3)	0.048 (2)	−0.030 (3)	−0.004 (2)	−0.004 (2)
C41	0.077 (2)	0.053 (2)	0.0423 (18)	−0.025 (2)	−0.0042 (17)	0.0015 (15)
C42	0.086 (3)	0.075 (3)	0.055 (2)	−0.045 (2)	0.0024 (19)	0.0052 (19)
C43	0.070 (2)	0.057 (2)	0.057 (2)	−0.028 (2)	−0.0150 (18)	0.0029 (17)
C44	0.108 (4)	0.091 (4)	0.095 (3)	−0.062 (3)	−0.034 (3)	0.010 (3)
C45	0.136 (5)	0.096 (4)	0.098 (4)	−0.064 (4)	−0.062 (4)	0.005 (3)
C46	0.112 (4)	0.100 (4)	0.072 (3)	−0.033 (3)	−0.046 (3)	−0.014 (3)
C47	0.075 (3)	0.085 (3)	0.054 (2)	−0.025 (2)	−0.0218 (19)	−0.006 (2)
C48	0.057 (2)	0.0462 (19)	0.0466 (18)	−0.0124 (16)	−0.0155 (15)	−0.0001 (15)
N1	0.0382 (14)	0.0564 (17)	0.0419 (14)	−0.0114 (13)	0.0045 (11)	−0.0060 (12)
N2	0.0426 (15)	0.0472 (17)	0.0515 (15)	−0.0077 (13)	−0.0094 (12)	−0.0022 (13)
N3	0.0585 (17)	0.0560 (18)	0.0450 (15)	−0.0226 (15)	−0.0069 (13)	−0.0018 (13)
O1	0.0431 (12)	0.0534 (15)	0.0454 (12)	−0.0039 (11)	0.0081 (10)	−0.0060 (10)
O2	0.0754 (17)	0.0670 (17)	0.0472 (13)	−0.0086 (14)	0.0170 (12)	0.0053 (12)
O3	0.0534 (14)	0.0623 (16)	0.0524 (14)	0.0052 (13)	−0.0057 (11)	−0.0006 (12)
O4	0.0723 (17)	0.0653 (18)	0.0621 (16)	0.0051 (14)	0.0163 (14)	−0.0081 (13)
O5	0.0611 (15)	0.0496 (15)	0.0467 (13)	−0.0168 (12)	0.0058 (11)	−0.0040 (11)
O6	0.0686 (16)	0.0710 (18)	0.0470 (13)	−0.0110 (14)	0.0193 (12)	−0.0040 (12)

C1—C2	1.388 (4)	C25—C26	1.411 (6)
C1—C6	1.389 (4)	C25—H25	0.9300
C1—C7	1.501 (4)	C26—C27	1.350 (6)
C2—C3	1.389 (4)	C26—H26	0.9300
C2—H2	0.9300	C27—C28	1.422 (5)
C3—C4	1.386 (4)	C27—H27	0.9300
C3—C8	1.488 (4)	C28—C29	1.386 (5)
C4—C5	1.379 (4)	C29—C30	1.386 (5)
C4—H4	0.9300	C29—H29	0.9300
C5—C6	1.397 (4)	C30—C31	1.424 (5)
C5—C9	1.503 (4)	C30—C35	1.430 (5)
C6—H6	0.9300	C31—C32	1.345 (6)
C7—O2	1.208 (4)	C31—H31	0.9300
C7—O1	1.308 (4)	C32—C33	1.405 (6)
C8—O4	1.208 (4)	C32—H32	0.9300
C8—O3	1.316 (4)	C33—C34	1.360 (6)
C9—O6	1.207 (4)	C33—H33	0.9300
C9—O5	1.304 (4)	C34—C35	1.414 (5)
C10—N1	1.349 (4)	C34—H34	0.9300
C10—C11	1.406 (5)	C35—N2	1.344 (4)
C10—C15	1.433 (4)	C36—N3	1.341 (4)
C11—C12	1.356 (6)	C36—C37	1.416 (5)
C11—H11	0.9300	C36—C41	1.426 (5)
C12—C13	1.411 (6)	C37—C38	1.344 (6)
C12—H12	0.9300	C37—H37	0.9300
C13—C14	1.337 (6)	C38—C39	1.403 (7)
C13—H13	0.9300	C38—H38	0.9300
C14—C15	1.427 (5)	C39—C40	1.339 (7)
C14—H14	0.9300	C39—H39	0.9300
C15—C16	1.377 (5)	C40—C41	1.425 (6)
C16—C17	1.395 (5)	C40—H40	0.9300
C16—H16	0.9300	C41—C42	1.376 (6)
C17—C18	1.412 (5)	C42—C43	1.382 (5)
C17—C22	1.430 (4)	C42—H42	0.9300
C18—C19	1.346 (6)	C43—C48	1.426 (5)
C18—H18	0.9300	C43—C44	1.427 (6)
C19—C20	1.400 (6)	C44—C45	1.343 (7)
C19—H19	0.9300	C44—H44	0.9300
C20—C21	1.351 (6)	C45—C46	1.401 (7)
C20—H20	0.9300	C45—H45	0.9300
C21—C22	1.424 (5)	C46—C47	1.350 (6)
C21—H21	0.9300	C46—H46	0.9300
C22—N1	1.348 (4)	C47—C48	1.407 (5)
C23—N2	1.348 (4)	C47—H47	0.9300
C23—C28	1.420 (5)	C48—N3	1.344 (4)
C23—C24	1.423 (5)	O1—H1	1.03 (4)
C24—C25	1.355 (6)	O3—H3	1.08 (6)
C24—H24	0.9300	O5—H5	1.10 (5)
C2—C1—C6	119.1 (2)	C27—C26—C25	120.5 (4)
C2—C1—C7	118.1 (3)	C27—C26—H26	119.7
C6—C1—C7	122.7 (3)	C25—C26—H26	119.7
C1—C2—C3	121.0 (3)	C26—C27—C28	120.4 (4)
C1—C2—H2	119.5	C26—C27—H27	119.8
C3—C2—H2	119.5	C28—C27—H27	119.8
C4—C3—C2	119.2 (3)	C29—C28—C23	117.6 (3)
C4—C3—C8	118.7 (2)	C29—C28—C27	123.3 (3)
C2—C3—C8	122.0 (3)	C23—C28—C27	119.1 (3)
C5—C4—C3	120.8 (3)	C28—C29—C30	120.6 (3)
C5—C4—H4	119.6	C28—C29—H29	119.7
C3—C4—H4	119.6	C30—C29—H29	119.7
C4—C5—C6	119.6 (3)	C29—C30—C31	123.7 (3)
C4—C5—C9	118.3 (2)	C29—C30—C35	118.2 (3)
C6—C5—C9	122.0 (3)	C31—C30—C35	118.1 (3)
C1—C6—C5	120.3 (3)	C32—C31—C30	120.9 (4)
C1—C6—H6	119.8	C32—C31—H31	119.6
C5—C6—H6	119.8	C30—C31—H31	119.6
O2—C7—O1	124.5 (3)	C31—C32—C33	120.4 (4)
O2—C7—C1	121.0 (3)	C31—C32—H32	119.8
O1—C7—C1	114.5 (3)	C33—C32—H32	119.8
O4—C8—O3	123.3 (3)	C34—C33—C32	121.6 (4)
O4—C8—C3	122.9 (3)	C34—C33—H33	119.2
O3—C8—C3	113.9 (3)	C32—C33—H33	119.2
O6—C9—O5	123.8 (3)	C33—C34—C35	119.4 (4)
O6—C9—C5	120.8 (3)	C33—C34—H34	120.3
O5—C9—C5	115.4 (2)	C35—C34—H34	120.3
N1—C10—C11	119.2 (3)	N2—C35—C34	118.6 (3)
N1—C10—C15	121.6 (3)	N2—C35—C30	121.9 (3)
C11—C10—C15	119.3 (3)	C34—C35—C30	119.5 (3)
C12—C11—C10	120.3 (3)	N3—C36—C37	119.3 (3)
C12—C11—H11	119.9	N3—C36—C41	122.0 (3)
C10—C11—H11	119.9	C37—C36—C41	118.6 (3)
C11—C12—C13	120.6 (4)	C38—C37—C36	120.3 (4)
C11—C12—H12	119.7	C38—C37—H37	119.8
C13—C12—H12	119.7	C36—C37—H37	119.8
C14—C13—C12	121.3 (4)	C37—C38—C39	121.5 (5)
C14—C13—H13	119.3	C37—C38—H38	119.2
C12—C13—H13	119.3	C39—C38—H38	119.2
C13—C14—C15	120.3 (3)	C40—C39—C38	120.1 (4)
C13—C14—H14	119.9	C40—C39—H39	119.9
C15—C14—H14	119.9	C38—C39—H39	119.9
C16—C15—C14	123.1 (3)	C39—C40—C41	121.1 (4)
C16—C15—C10	118.6 (3)	C39—C40—H40	119.4
C14—C15—C10	118.3 (3)	C41—C40—H40	119.4
C15—C16—C17	120.4 (3)	C42—C41—C40	124.5 (3)
C15—C16—H16	119.8	C42—C41—C36	117.3 (3)
C17—C16—H16	119.8	C40—C41—C36	118.2 (4)
C16—C17—C18	123.3 (3)	C41—C42—C43	121.7 (3)
C16—C17—C22	117.8 (3)	C41—C42—H42	119.1
C18—C17—C22	118.8 (3)	C43—C42—H42	119.1
C19—C18—C17	120.4 (4)	C42—C43—C48	117.4 (3)
C19—C18—H18	119.8	C42—C43—C44	124.6 (4)
C17—C18—H18	119.8	C48—C43—C44	118.0 (4)
C18—C19—C20	121.1 (4)	C45—C44—C43	120.9 (4)
C18—C19—H19	119.4	C45—C44—H44	119.5
C20—C19—H19	119.4	C43—C44—H44	119.5
C21—C20—C19	121.1 (4)	C44—C45—C46	120.4 (4)
C21—C20—H20	119.4	C44—C45—H45	119.8
C19—C20—H20	119.4	C46—C45—H45	119.8
C20—C21—C22	119.8 (3)	C47—C46—C45	121.1 (4)
C20—C21—H21	120.1	C47—C46—H46	119.4
C22—C21—H21	120.1	C45—C46—H46	119.4
N1—C22—C21	119.2 (3)	C46—C47—C48	120.4 (4)
N1—C22—C17	122.2 (3)	C46—C47—H47	119.8
C21—C22—C17	118.7 (3)	C48—C47—H47	119.8
N2—C23—C28	122.9 (3)	N3—C48—C47	119.3 (3)
N2—C23—C24	118.3 (3)	N3—C48—C43	121.7 (3)
C28—C23—C24	118.8 (3)	C47—C48—C43	119.0 (3)
C25—C24—C23	120.0 (4)	C22—N1—C10	119.3 (2)
C25—C24—H24	120.0	C35—N2—C23	118.8 (3)
C23—C24—H24	120.0	C36—N3—C48	119.7 (3)
C24—C25—C26	121.2 (4)	C7—O1—H1	108 (2)
C24—C25—H25	119.4	C8—O3—H3	111 (3)
C26—C25—H25	119.4	C9—O5—H5	112 (3)
C6—C1—C2—C3	1.0 (4)	N2—C23—C28—C27	−179.6 (3)
C7—C1—C2—C3	178.6 (3)	C24—C23—C28—C27	−0.1 (4)
C1—C2—C3—C4	−0.1 (4)	C26—C27—C28—C29	179.2 (3)
C1—C2—C3—C8	−176.5 (3)	C26—C27—C28—C23	−1.0 (5)
C2—C3—C4—C5	−0.7 (4)	C23—C28—C29—C30	0.5 (4)
C8—C3—C4—C5	175.8 (3)	C27—C28—C29—C30	−179.7 (3)
C3—C4—C5—C6	0.6 (4)	C28—C29—C30—C31	179.8 (3)
C3—C4—C5—C9	−177.8 (3)	C28—C29—C30—C35	−0.4 (4)
C2—C1—C6—C5	−1.2 (4)	C29—C30—C31—C32	179.9 (4)
C7—C1—C6—C5	−178.7 (3)	C35—C30—C31—C32	0.1 (5)
C4—C5—C6—C1	0.4 (4)	C30—C31—C32—C33	0.2 (6)
C9—C5—C6—C1	178.7 (3)	C31—C32—C33—C34	−0.8 (7)
C2—C1—C7—O2	4.4 (5)	C32—C33—C34—C35	1.0 (6)
C6—C1—C7—O2	−178.1 (3)	C33—C34—C35—N2	180.0 (3)
C2—C1—C7—O1	−176.0 (3)	C33—C34—C35—C30	−0.7 (5)
C6—C1—C7—O1	1.6 (4)	C29—C30—C35—N2	−0.3 (4)
C4—C3—C8—O4	6.9 (5)	C31—C30—C35—N2	179.5 (3)
C2—C3—C8—O4	−176.7 (3)	C29—C30—C35—C34	−179.6 (3)
C4—C3—C8—O3	−173.1 (3)	C31—C30—C35—C34	0.1 (5)
C2—C3—C8—O3	3.3 (4)	N3—C36—C37—C38	178.3 (4)
C4—C5—C9—O6	−7.2 (5)	C41—C36—C37—C38	−0.4 (7)
C6—C5—C9—O6	174.5 (3)	C36—C37—C38—C39	0.6 (8)
C4—C5—C9—O5	173.2 (3)	C37—C38—C39—C40	−0.8 (9)
C6—C5—C9—O5	−5.1 (4)	C38—C39—C40—C41	0.7 (8)
N1—C10—C11—C12	−178.8 (4)	C39—C40—C41—C42	178.7 (5)
C15—C10—C11—C12	0.7 (6)	C39—C40—C41—C36	−0.5 (7)
C10—C11—C12—C13	0.7 (7)	N3—C36—C41—C42	2.4 (6)
C11—C12—C13—C14	−1.0 (8)	C37—C36—C41—C42	−178.9 (4)
C12—C13—C14—C15	−0.2 (7)	N3—C36—C41—C40	−178.4 (4)
C13—C14—C15—C16	−179.1 (4)	C37—C36—C41—C40	0.3 (6)
C13—C14—C15—C10	1.5 (6)	C40—C41—C42—C43	−179.6 (4)
N1—C10—C15—C16	−1.7 (5)	C36—C41—C42—C43	−0.4 (6)
C11—C10—C15—C16	178.9 (3)	C41—C42—C43—C48	−0.6 (6)
N1—C10—C15—C14	177.7 (3)	C41—C42—C43—C44	179.2 (4)
C11—C10—C15—C14	−1.8 (5)	C42—C43—C44—C45	−178.5 (5)
C14—C15—C16—C17	−179.3 (3)	C48—C43—C44—C45	1.4 (7)
C10—C15—C16—C17	0.0 (5)	C43—C44—C45—C46	0.0 (9)
C15—C16—C17—C18	−179.8 (3)	C44—C45—C46—C47	−3.1 (9)
C15—C16—C17—C22	1.2 (5)	C45—C46—C47—C48	4.7 (8)
C16—C17—C18—C19	−179.0 (4)	C46—C47—C48—N3	177.2 (4)
C22—C17—C18—C19	0.0 (6)	C46—C47—C48—C43	−3.2 (6)
C17—C18—C19—C20	−0.5 (7)	C42—C43—C48—N3	−0.3 (6)
C18—C19—C20—C21	1.7 (7)	C44—C43—C48—N3	179.8 (4)
C19—C20—C21—C22	−2.4 (7)	C42—C43—C48—C47	−180.0 (4)
C20—C21—C22—N1	−178.8 (4)	C44—C43—C48—C47	0.2 (6)
C20—C21—C22—C17	1.9 (6)	C21—C22—N1—C10	−180.0 (3)
C16—C17—C22—N1	−0.9 (5)	C17—C22—N1—C10	−0.7 (5)
C18—C17—C22—N1	180.0 (3)	C11—C10—N1—C22	−178.6 (3)
C16—C17—C22—C21	178.4 (3)	C15—C10—N1—C22	2.0 (5)
C18—C17—C22—C21	−0.7 (5)	C34—C35—N2—C23	−179.7 (3)
N2—C23—C24—C25	−178.9 (3)	C30—C35—N2—C23	1.0 (4)
C28—C23—C24—C25	1.6 (5)	C28—C23—N2—C35	−1.0 (4)
C23—C24—C25—C26	−2.0 (5)	C24—C23—N2—C35	179.5 (3)
C24—C25—C26—C27	0.9 (6)	C37—C36—N3—C48	178.0 (4)
C25—C26—C27—C28	0.7 (6)	C41—C36—N3—C48	−3.3 (5)
N2—C23—C28—C29	0.2 (4)	C47—C48—N3—C36	−178.1 (3)
C24—C23—C28—C29	179.7 (3)	C43—C48—N3—C36	2.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	1.03 (4)	1.62 (4)	2.643 (4)	173 (4)
O3—H3···N2	1.08 (6)	1.55 (6)	2.619 (4)	166 (5)
O5—H5···N3	1.10 (5)	1.57 (5)	2.659 (4)	171 (6)
C14—H14···O6i	0.93	2.44	3.266 (5)	147
C16—H16···O6i	0.93	2.55	3.355 (5)	145
C18—H18···O2ii	0.93	2.54	3.389 (5)	151
C24—H24···O5iii	0.93	2.53	3.278 (5)	138
C27—H27···O4iv	0.93	2.59	3.435 (5)	151
C47—H47···O3iii	0.93	2.56	3.345 (5)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	1.03 (4)	1.62 (4)	2.643 (4)	173 (4)
O3—H3⋯N2	1.08 (6)	1.55 (6)	2.619 (4)	166 (5)
O5—H5⋯N3	1.10 (5)	1.57 (5)	2.659 (4)	171 (6)
C14—H14⋯O6i	0.93	2.44	3.266 (5)	147
C16—H16⋯O6i	0.93	2.55	3.355 (5)	145
C18—H18⋯O2ii	0.93	2.54	3.389 (5)	151
C24—H24⋯O5iii	0.93	2.53	3.278 (5)	138
C27—H27⋯O4iv	0.93	2.59	3.435 (5)	151
C47—H47⋯O3iii	0.93	2.56	3.345 (5)	143

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .